


So I Heard You Want to Be a Matchmaker (Hint: Don't Do This)

by Pugglemuggle



Category: Supernatural
Genre: Alternate Universe - Canon Divergence, Christmas, Christmas Fluff, Destiel Advent Calendar, Destiel Advent Calendar 2014, Feel-good, Fluff, Holidays, M/M, Matchmaking, SO MUCH FLUFF, Team Free Will, just basically happy stuff
Language: English
Status: Completed
Published: 2014-12-23
Updated: 2014-12-23
Packaged: 2018-03-03 00:43:43
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,721
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2831957
Author URL: https://archiveofourown.org/users/Pugglemuggle/pseuds/Pugglemuggle
Summary: <blockquote class="userstuff">
              <p>“So wait, they seriously haven’t hooked up yet?”</p>
            </blockquote>





	So I Heard You Want to Be a Matchmaker (Hint: Don't Do This)

**Author's Note:**

> This was written for the [2014 Destiel Advent Calendar](http://destieladventcalendar.tumblr.com/). Enjoy!

“So wait, they seriously haven’t hooked up yet?”

Charlie leaned in confidingly across the table towards Sam and Kevin, her voice a loud whisper. Dean and Cas had just left the Men of Letter’s library— _together—_ and they’d even closed the door behind them, if that wasn’t enough.

In reply, Sam just gave Charlie a grim little shrug.

“Wow…” she said, leaning back again. “I mean, I just thought­—you know, with the way Dean talked about him—that they’d be…. I don’t know, I guess I’ve only just met Cas, but…. And in the _books—”_

“The books?” Kevin interrupted. Sam filled him in.

“A friend of ours, Chuck—well, sort of a friend, not exactly…” Sam paused, but shook his head and continued. “Anyway, he was a prophet, until… uh, you, I guess. He wrote this series of books about our lives, and he didn’t publish all of them, but I guess that Charlie says the rest of it has been put up online…?”

“Yup,” said Charlie. “Forever.”

“Yeah…” Sam sighed. Then, “Wait, what do the books say about Cas and Dean?”

Charlie snorted and rolled her eyes, wrapping her fingers around her mug of hot cocoa. “Everything. I mean, it never explicitly said, ‘Oh hey, Dean and Cas are in love and they want to sex it up like nobody’s business’ but I think everyone thought it was pretty clear, especially in _Free to Be You and Me_ after Dean took Cas to that strip bar, oh _man_ ….”

“Dean took… _Cas_ , to a strip bar?” Sam asked.

“Yeah, right after Lucifer had been let out, and you two split up for a little while. I think you went to work at a restaurant or something?”

“Oh…”

“So…” said Kevin, scooting closer to the table and setting his hands in front of him in a business-like manner, “either the Chuck guy was seriously exaggerating some stuff to lead on his readership—”

“Everything he wrote was actually scarily accurate,” Sam interjected.

“—or,” Kevin continued, undaunted, “they’re completely helpless and need someone to facilitate for them.”

“Gentlemen,” Charlie said with a grin, “I think we have work to do.”

⚹❄⚹

“So…” Charlie said, doing her best to sound nonchalant. Since she and Dean were the only two with any real enthusiasm about Christmas, it had fallen to them to decorate the library, which they’d spent the better part of their morning trying to do. “Castiel, huh? He seems… nice.”

Dean looked sidelong at her, like he was already starting to suspect that something was up. Dammit, she was really bad at matchmaking….

“Cas is… a really good guy,” said Dean carefully.

Charlie nodded encouragingly. “Dreamy?”

Dean stopped what he was doing and turned to look at her straight on. “You’ve said that before.”

“Yeah. Because he is, you know, dreamy.”

“I thought you weren’t into his kind of parts.”

“I’m not, but…”

“…But?”

“But I don’t have to be into guys to know that he’s dreamy.”

“O…kay…” said Dean, his brow creased. “Glad we got that sorted out.”

“Just sayin’.”

“Yeah. Sure.”

“Okay.”

Needless to say, Charlie’s first attempt at talking Cas up proved unsuccessful.

⚹❄⚹

Sam knew his brother better than anyone. He knew instinctively when Dean was lying, and when he was being cryptic, and when he was intentionally leaving things out of a conversation. Right now, he was pretty damn sure Dean was doing all three.

“You and Cas get a lot of research done yesterday?” Sam asked conversationally. He already knew the answer—it was no. The books he’d given them to look through the day before were in exactly the same place he’d left them.

“Yeah, tons of research,” said Dean anyway. “Didn’t find anything, though. Nothing we can use.”

“…Right, okay.”

A couple moments of silence. Sam jotted down a few more notes from _Beasts of Aborigine Lore_.

“You and Cas seem to be really, uh, productive,” Sam pressed again.

“Yep.”

“You never used to like research, Dean.”

“Yeah, and I still don’t,” said Dean, gesturing to the tome in front of him and his sad half-page of notes. “But it’s a little better when you’re not working with the Spanish inquisition, Jesus….”

“I’m just… making conversation.”

“Yeah, well, you’re being….” Dean made an ambiguous gesture that Sam guessed was supposed to mean something along the lines of ‘irritating’ or ‘difficult’.

Sam shook his head “Well, I’m glad you and Cas work so well together….”

Dean shot him a suspicious look but didn’t continue the line of discussion. This was impossible.

⚹❄⚹

“Cas…” began Kevin. Dean looked up, his expression vaguely perturbed.

“Yeah?”

Kevin paused.

“You know what, never mind.”

Kevin was not cut out for this kind of job. He’d leave that to the professionals.

⚹❄⚹

“Maybe we’re going about this the wrong way,” Sam suggested.

“Yeah,” Charlie agreed. “We’ve been targeting Dean, but maybe we should’ve been targeting Cas.”

Kevin shook his head. “You sure? Cas seems like he’d be even more oblivious than Dean.”

“Maybe…” Sam conceded. “The other day I saw Cas walk out of Dean’s room in the middle of the night, and he told me he’d wanted to ask Dean what kind of shampoo he should buy in the morning.”

Charlie began to giggle, covering her mouth with her hand in an attempt to stifle the noise. “You’re joking. You _have_ to be joking.”

“I’m not!” said Sam, starting to grin. “A few weeks ago he was doing some kind of angel reconnaissance for a couple days, and then he just showed up out of the blue, handed Dean a cherry pie, said something like ‘I hope you enjoy this pastry’, and then disappeared for a few more days.”

“I remember that,” Kevin added.

“How are they _not_ a couple?” asked Charlie. “How are they not hooking up _all the time_?”

“Do you remember a few days ago when he bought Dean that porn magazine?”

“Yeah…” said Sam, running a hand through his hair. “Cas has… no boundaries. No concept of privacy, either. Maybe we should keep trying with Dean—”

“Wait,” Charlie interrupted him. “Cas doesn’t get privacy. We could use that.”

“What do you mean?” Sam asked warily.

Kevin shook his head. “If you’re thinking what I think you’re thinking….”

“It’s brilliant and you know it,” Charlie insisted, pointing an accusing finger at Kevin. “Now, Sam, here’s the plan….”

⚹❄⚹

“Hey, I’m going to take a shower, just in case anyone starts looking for me,” Dean announced, towel in hand.

“Go ahead, knock yourself out,” said Sam casually without looking up from his laptop. As soon as Dean’s footsteps left the room, though, Sam sat up and snapped the computer shut. The others—Charlie and Kevin—looked up.

“Should we do it now?” Charlie asked quietly, glancing down the hall towards Cas’s room.

Kevin shook his head. “No, let’s wait a few minutes at least.”

“Okay.”

Sam was pretty sure they only waited one minute.

Charlie got to her feet, rubbing her hands on her thighs. “You think we’re good to go? I think we’re good to go.”

“Sure. Let’s do it,” Sam said, standing. Kevin followed suit, and they both followed Charlie out of the room, towards the hall where Castiel’s room was.

“Okay, you two need to go hide somewhere—your room, Sam?”

Sam nodded and pulled Kevin into his room, just across the hall from Dean’s and diagonal to Cas’s. They waited with the door mostly closed as Charlie raised a tentative hand to knock at Castiel’s door.

“Hey, Cas?” she called. A moment later, the angel appeared in the doorway.

“Yes, Charlie?” he said. “Is there… something you wanted from me?”

“Actually, yes…” she replied, just like they’d planned. “I was hoping you could do me a favor.”

“A favor?”

“Yeah, uh, you see, Dean’s taking a shower right now, but I left my toothbrush in that bathroom. Do you think you could grab it for me?”

Castiel looked understandably confused.

“Is there a reason why you don’t want to get it yourself?” he asked her.

“Oh, well, I’m really not into naked guys. Lesbian, remember? I try to avoid them when I can,” Charlie said. Hearing her say their excuse aloud made it sound transparent and flimsy. Sam started to have doubts. Cas was pretty oblivious, but he couldn’t be _that_ oblivious.

Sam’s doubts, however, proved to be unfounded. Without any further questions, Cas said, “Of course,” and went directly down the hall towards the bathroom.

“It’s the Sonic Screwdriver one! Kinda big, kinda white and brownish, I guess,” she called after him. All three of them watched as turned the corner towards the bathroom, where the sound of running water was drifting down the hall.

“Do you think Dean’ll let him get away with it?” Charlie asked.

“No,” Sam said honestly. “He’ll probably yell.”

Sure enough, there was a loud, “Hey!” from the direction of the bathroom, followed by the hasty turning off of the water. Castiel rounded the corner, seeming unperturbed.

“Here is your toothbrush,” Castiel said to Charlie, handing her the screwdriver. She accepted it mutely just before a pink-faced Dean came barging around the corner, hastily wrapping a towel around his waist.

“What the hell, Cas?”

“Charlie… wanted her toothbrush.” Cas said, brow furrowing.

“Yeah, but I was showering in there.”

“There was a shower curtain.”

“But… still, that’s a little…” Dean trailed off, suddenly seeming to notice that all four of them were looking at him. “I dunno, it’s weird, Cas. Just… knock or something, ‘kay?”

He turned around and went back the way he came. Cas went back into his room and shut the door.

“I couldn’t tell if he was blushing or just red from the shower….” Charlie mused. “Either way, I think we need to step up our game. That didn’t really work very well.”

⚹❄⚹

“Are you sure these are the right kind, Sam?” Castiel asked, holding the pot in front of him like he was concerned the flowers would spontaneously combust.

“Yeah, no, Dean loves poinsettias. Has ever since we were kids,” Sam assured him. “Thanks for getting them, Cas. You should go show ‘em to Dean.”

“Yes, I’ll show him.”

Sam and Kevin watched as Cas walked into the library where Dean was still doing “research” without actually touching the books or the computer. As soon as Cas got closer, Dean sat up and stared.

“What’s that?” he said, the words sounding less like a question and more like a demand.

“They’re poinsettias,” Cas supplied helpfully. “They’re a species native to Mexico and Central America that are commonly used in Christmas floral decorations, and—”

“No, wait Cas, I didn’t mean… I know what poinsettias are, I just wondered why you got them.”

“I thought we were trying to make the bunker more… festive.”

“We are.”

“I was also told that you like this particular kind of plant.”

“I….” Dean paused. “Uh, yeah, I do. I guess. I mean, I do like them. I was just…. Never mind. Thanks for, uh, yeah. Thanks.”

“You’re always welcome, Dean.”

“Yeah, uh…” Dean was rubbing the back of his neck in the way he did when he was embarrassed, but then he stopped, seeming to consider something. “Who… Who told you I liked poinsettias?”

“Sam,” Cas answered easily. Sam swore and tried to walk casually out of sight before Dean noticed him, but judging by the tone of Dean’s voice, he was fairly certain he hadn’t succeeded.

“Sam, huh?” Dean’s loud, irritated voice followed him down the hall. “Well, then, I’ll have to make sure to talk to him, too. Tell him thanks for me! Thanks a lot!”

⚹❄⚹

“Guys, I think Dean is onto us,” said Charlie the next day.

Kevin gave her a look. “Well, we haven’t exactly been subtle….”

“Yeah, I know, I know, but did you see the look he gave me this morning when I stole his seat at breakfast? I mean, it worked. He still sat next to Cas. But he was definitely giving me a look.”

“Are you sure the look was about the seats?” Sam asked. “Maybe he found out about the, uh, video you showed Cas yesterday.”

“The Christmas porno? No, not unless Cas told him about it.”

“At least the cookie decorating thing seemed to work,” Kevin said diplomatically. “They got really into that.”

Charlie nodded, grinning like a madwoman. “Yeah, I think we can count that as a success. Did you see them after we left? Did you see Cas’s face? He had frosting all the way down his—”

“I thought Cas said he’d just accidentally got some smeared on his coat sleeve.”

“Yeah, sure. That’s not what I saw.”

“Is there anything else we can try?” Sam asked the other two. “Tomorrow’s Christmas Eve….”

Kevin looked thoughtful. “Well,” he said, “there is one other thing….”

⚹❄⚹

“So,” Charlie said, holding the two DVD cases in front of her, “should we watch _A Christmas Story_ or _Miracle on 34 th Street_?”

“A Christmas Story,” Dean said immediately.

“Miracle on 34th Street,” said Kevin. “I’ve seen the other one way too many times.

“Yeah, I’m with Kevin,” Charlie agreed. “Sorry, Dean. Miracle on 34th Street it is, then, unless Cas or Sam wants to vote…?”

Sam held up his hands conciliatorily. “I’m fine with either of them. I don’t mind.”

“Cas…?”

“C’mon, Cas, vote for my one. It’s funny. The other one’s boring,” Dean pushed. “You’ll like mine.”

Cas seemed to debate the topic for a moment before saying, slowly, “I will vote for Dean’s movie.”

“So it’s a tie,” Charlie announced. “Let’s coin-flip this bitch.”

Heads was _A Christmas Story_ , and tails was _Miracle on 34 th Street_. The coin landed tails.

“I _believe_ ,” said Charlie with a grin, “that Kevin and I win. Miracle it is.”

⚹❄⚹

Sam, Kevin, and Charlie made sure to take every seat besides the couch, so Dean and Cas were forced to sit next to each other. They didn’t seem to notice the manipulation of the seating arrangement, thankfully—apparently they’d been subtle enough this time. About a quarter of the way into the movie, Cas and Dean were sitting close enough that half the couch was empty. When the movie passed the half-way point, their legs were pressed together on the couch, and Dean was almost completely asleep, his head tossed back over the back of the couch and his arm slung haphazardly over Cas’s shoulder. That’s how the three of them left them, slowly trickling out, one by one, coming up with excuses until Dean and Cas were left alone.

When Kevin decided to check back in on them before going to bed, neither of them had moved.

⚹❄⚹

“Thanks, Charlie. I needed a laugh,” Dean said the next morning—Christmas morning—as he held up the inappropriately labeled bottle of hand sanitizer. “That’s actually really funny.”

“No problem, Dean. Thanks for the swords,” Charlie replied. They were the samurai swords from the bunker, Sam knew. Dean had caught Charlie eyeing them the first day she’d arrived, and since then he’d had them set aside to give to her. Sam couldn’t think of a better person to give them to.

“Careful with them though, okay?” Dean warned. “They’re sharp. Like, really sharp.”

“Sure thing, Dean.”

“Hey, Cas? Do you mind helping me in the kitchen for a minute?” Sam called.

Cas got to his feet, Dean’s too-large AC/DC shirt slipping close to one shoulder. “Of course, Sam,” he replied.

They’d asked about the shirt, of course. Charlie had been the most blunt about it: “Why is Cas wearing your shirt?” Dean’s answer had actually been surprisingly well-supported. He’d said that since Cas didn’t have anything to wear to sleep, since he didn’t actually sleep, and the only clothes he owned were his suit, pants, coat, and tie, that he should borrow some of their clothes. Seeing as Dean was the closest to Cas’s size, it made sense that he should be the one lending him the stuff. And besides, Dean had said, it was a good way to expose Cas to good music. Osmosis, maybe.

Cas left the room, leaving Dean, Kevin, and Charlie in a sea of crumpled wrapping paper. They started cleaning it up, Kevin and Charlie keeping an eye on their speed. When all the paper had been shoved into a paper gift bag, they sent Dean out towards the kitchen to get rid of it. It all went according to plan. Their timing was impeccable.

Just as Cas was walking out of the kitchen, Dean was walking into it. They met in the middle, right under the doorway. They would have kept walking their opposite ways if Charlie hadn’t shouted, “Mistletoe!”

Dean froze, but Cas just looked confused. “…Mistletoe?” he asked.

“Right above you, Sam said apologetically, appearing just beyond the doorway and gesturing upward. You two are stuck under it.”

“I don’t understand,” said Cas. Dean was fidgeting, and even though he was looking at the floor, Sam could tell that his cheeks were flushed.

“When two people get stuck under mistletoe,” said Charlie helpfully, “they have to kiss.”

Apparently, that was the last straw for Dean.

“You know, guys, I know what you’re doing, and I really don’t appreciate it,” Dean said loudly, looking at each of them in turn. “You’ve been doing this all week—don’t even deny it, I know you have. I’m really tired of it. Cut it out, would you? Nothing’s going on between me and Cas. This is none of your goddamn business, anyway. Come on, Cas. Let’s go.”

Dean grabbed Cas’s arm and pulled him out through the bunker kitchen, heading towards the hallway. The others watched them leave in stunned silence. Finally, Charlie spoke up.

“Well,” she said, “that was a little overdramatic.”

⚹❄⚹

“Maybe we should give up on the whole thing,” Kevin suggested. “Maybe we’re just reading too much into this.”

Charlie shook her head and waved her hand dismissively. “No. No way. There is something going on between them. You don’t act like when you’re completely platonic. There’s no way.”

“I don’t know,” Kevin said. “Cas is an angel. Maybe things are different for him. Maybe his idea of relationships is just a lot deeper than what we think of.”

“But you don’t _do_ those things with people unless there’s something going on! You just don’t act like that! You don’t smear frosting over each other’s faces, and you don’t get tongue-tied when they give you flowers, and you don’t freak out when they invade your shower space. You don’t go out of your way to give them a pie in the middle of a mission, and you don’t _look_ at them like that. You don’t have a whole series where they do nothing but stare at each other soulfully and sacrifice their lives for each other without having _some_ part of it be at least a little bit romantic!”

“Chuck was pretty descriptive…” Sam agreed.

“I guess what I’m saying,” Charlie said, “is that these kinds of things don’t just… happen. They all have a cause, a reason. I think they love each other. A lot. That’s the reason.”

“I think we should apologize to them,” Sam said seriously. “Whether or not you’re right, Charlie, Dean’s also sort of right. It’s not really any of our business….”

“Yeah, I know,” Charlie agreed, deflating somewhat. “You’re right. Let’s go say sorry….”

They made their way down the hallway, in the direction of Dean and Cas’s rooms. That’s where they guessed they would have gone, but they couldn’t be sure—the whole wing was silent. Except… there was some soft shuffling coming from Dean’s room. That must be where Dean was, Sam figured. He knocked on the door once, quickly, out of habit more than anything, and then turned the handle, swinging the door open, and—

“Holy….”

That was _not_ what he had been expecting.

“I _was_ right,” Charlie said, sounding pleased. Kevin turned around immediately and stared at the opposite wall.

A bare-chested Dean was quickly trying—and failing—to pull his pants up, while Cas sat up slowly from Dean’s bed, the mostly-naked picture of imperturbable serenity. He gave each of them a mildly confused look. At least he had the graces to pull a pillow over his lap by the time Dean finally succeeded in zipping his jeans.

“What—What the hell are you doing here?” Dean demanded, and if his face hadn’t been red earlier (which it definitely had been), then it was red beyond doubt now.

“We were going to apologize for butting into all your stuff…” Sam said, “…but now that we’re here, do you want to tell me how long _this_ ”—he gestured between Dean and Cas—“has been going on?”

Dean said, “Just a few weeks.”

At the same time, Cas said, “A couple months.”

“You’ve been doing this for _months_ , and we never noticed? How?”

“Dean can be very quiet,” Castiel supplied helpfully. “Also, you all seemed to think that our behavior towards each other was due to our extreme compatibility rather than any kind of preexisting relationship. That made it easier.”

“You hid in plain sight?” Charlie said. “That’s… actually very impressive.”

“Yeah, I guess you could… say that…” Dean conceded. “I’m—I, uh, shouldn’t have snapped at you guys just now. I just…. I didn’t want you making a big deal out of this, like you would—like you are doing, right now. Don’t deny it.

“Yeah, you’re probably right,” Sam concluded. “But sometimes making a big deal out of something isn’t so bad, especially when, you know, it’s a big deal.”

“Point taken,” Dean agreed. The tension started to seep back into the room, and something was telling them that it wasn’t a good idea to stick around for much longer.

“So, we should let you guys get back to…” Charlie started, then broke off. “Well, whatever you were doing. Have fun.”

Charlie, Sam, and Kevin quickly backed out of the door and shut it behind them, walking towards the library.

“That was—”

“Really unexpected? Awkward? Impressive?”

“Yeah,” Kevin said. “Yeah, all three.”

⚹❄⚹

In the end, they hadn’t had to do a thing. A matchmaker called Fate had done all the work for them back in a barn in Pontiac, Illinois.

Some things were just meant to be.


End file.
